If Times Are Tough — Don’t Hide. Be Present.
What I see CEOs at struggling start-ups do: – Go dark– Hide– Lash out– Tweet about lots of things non-work– Invest time on tiny expenses– Argue internally What should do: – Be Present– Be Honest– Be the Rock–...
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep?
Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview …...
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make?
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre...
Dear SaaStr: What Was The Best Advice You Ever Got From an Angel Investor
Dear SaaStr: What Was The Best Advice You Ever Got From an Angel Investor The best advice I ever got from one of my angel investors: Stop feeling sorry for yourself. I went to meet with one of my angels and mentors when things were probably toughest at my last...
7 Of The Top Things Founders Get Wrong When They Start a B2B Company
Dear SaaStr: What do startup founders typically get wrong when starting a business? My list: Not committing to 24 months upfront to getting to Real Revenues and a Minimum Sellable Product. We’ve written about this before, but I see it again and again and again. It...
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk?
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk? It if’s that bad — it’s just not going to work. The issue isn’t so much that he’s a complete jerk. Maybe he is, maybe he isn’t, or most likely, it’s somewhere in the...
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a B2B Startup?
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a B2B Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code...
Five “Cons” To Adding a Free Edition
Dear SaaStr: Is There Any “Con” In Giving Our Sales Tool For Free to Early-Stage Startups? Free can absolutely work. Done right, it’s built some of the biggest companies in B2B + AI: ChatGPT. Claude. Cursor. Slack. Zoom. Canva. Notion. Figma. Almost...
Dear SaaStr: How Do You Sell B2B Products to Bigger Enterprise Customers?
Dear SaaStr: How Do You Sell B2B Products to Bigger Enterprise Customers? You solve their problems. Large enterprises use lots of tools, widgets, and pieces of software in their businesses, but they tend to use the obvious, trusted solutions. They aren’t looking for a...
Dear SaaStr: Is It Worth Working as a Sales Rep?
Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2...
What To Do When A Customer Wants to Cancel A Contract
Hopefully, 100% of your customers love you. But as time goes on, you’ll oversell a few deals. Or not quite deliver in some fashion. Or fail to deploy in others. And some customers will ask for their money back. When they e-signed binding, good old-fashioned...
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated?
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated? The part I didn’t originally get as a first-time B2B founder was how relatively easy it is to grow exising accounts and account size if your customers are happy. 120% NRR: Your revenue...
Dear SaaStr: What Do You Do With Churned Customers?
Dear SaaStr: What Do You Do With Churned Customers? You put them into a Get Them Back bucket and re-market to them with a dedicated program. And you have sales especially follow-up twice. Once in about 90 days, to see if they might want to come back —...
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
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